CA2374251C - Preparation et utilisation de liquides ioniques dans des transformations chimiques assistees par micro-ondes - Google Patents

Preparation et utilisation de liquides ioniques dans des transformations chimiques assistees par micro-ondes Download PDF

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Publication number
CA2374251C
CA2374251C CA002374251A CA2374251A CA2374251C CA 2374251 C CA2374251 C CA 2374251C CA 002374251 A CA002374251 A CA 002374251A CA 2374251 A CA2374251 A CA 2374251A CA 2374251 C CA2374251 C CA 2374251C
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Prior art keywords
ionic liquid
microwave
alkyl
cation
organic
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Expired - Fee Related
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CA002374251A
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CA2374251A1 (fr
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Jacob Westman
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Biotage AB
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Biotage AB
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J19/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
    • B01J19/08—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor
    • B01J19/12—Processes employing the direct application of electric or wave energy, or particle radiation; Apparatus therefor employing electromagnetic waves
    • B01J19/122—Incoherent waves
    • B01J19/126—Microwaves
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B39/00—Halogenation
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
    • C07B61/00—Other general methods
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/09—Preparation of ethers by dehydration of compounds containing hydroxy groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
    • C07C45/46—Friedel-Crafts reactions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Physics & Mathematics (AREA)
  • Electromagnetism (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Physical Or Chemical Processes And Apparatus (AREA)
  • Indole Compounds (AREA)

Abstract

Il est possible de préparer rapidement et efficacement des liquides ioniques par des transformations assistées par micro-ondes L'invention porte sur un procédé d'exécution de réactions assistées par micro-ondes, dont des réactions d'alkylation, utilisant des liquides ioniques comme solvants et donnant un rendement élevé et des temps de réaction considérablement réduits. Les liquides ioniques, utilisés comme additifs ou co-solvants, pour permettre le chauffage assisté par micro-ondes, de réactions chimiques exécutées dans des solvants organiques traditionnels, le plus souvent non polaires.
CA002374251A 1999-05-26 2000-05-26 Preparation et utilisation de liquides ioniques dans des transformations chimiques assistees par micro-ondes Expired - Fee Related CA2374251C (fr)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
DKPA199900734 1999-05-26
DKPA199900734 1999-05-26
PCT/IB2000/000719 WO2000072956A1 (fr) 1999-05-26 2000-05-26 Preparation et utilisation de liquides ioniques dans des transformations chimiques assistees par micro-ondes

Publications (2)

Publication Number Publication Date
CA2374251A1 CA2374251A1 (fr) 2000-12-07
CA2374251C true CA2374251C (fr) 2007-11-27

Family

ID=8096936

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002374251A Expired - Fee Related CA2374251C (fr) 1999-05-26 2000-05-26 Preparation et utilisation de liquides ioniques dans des transformations chimiques assistees par micro-ondes

Country Status (11)

Country Link
US (1) US6596130B2 (fr)
EP (1) EP1194227B1 (fr)
JP (1) JP2003500460A (fr)
CN (1) CN1188211C (fr)
AT (1) ATE276043T1 (fr)
AU (1) AU774290B2 (fr)
CA (1) CA2374251C (fr)
DE (1) DE60013832T2 (fr)
ES (1) ES2228518T3 (fr)
NO (1) NO321962B1 (fr)
WO (1) WO2000072956A1 (fr)

Families Citing this family (42)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7112450B2 (en) 2000-05-08 2006-09-26 Personal Chemistry I Uppsala Ab Method for performing multiple chemical reactions and a kit and system therefor
WO2002094883A2 (fr) 2001-01-22 2002-11-28 Covalent Associates, Inc. Procede en une etape de preparation de sels hydrophobes exempts d'halogenure
FI116142B (fi) * 2003-09-11 2005-09-30 Kemira Oyj Esteröintimenetelmä
FI116140B (fi) * 2003-12-03 2005-09-30 Kemira Oyj Eetteröintimenetelmä
EP1577281A1 (fr) * 2004-03-19 2005-09-21 Bayer CropScience GmbH Procédé de préparation de bibliothèques combinatoires
KR100739452B1 (ko) 2004-04-29 2007-07-18 인하대학교 산학협력단 α-알킬피롤 화합물의 제조방법
JP2006035078A (ja) * 2004-07-26 2006-02-09 National Institute Of Advanced Industrial & Technology マイクロ波照射による超臨界流体抽出分離方法及びその装置
DE102004040016A1 (de) * 2004-08-16 2006-02-23 Friedrich-Schiller-Universität Jena Verfahren zur Herstellung ionischer Flüssigkeiten
GB0500028D0 (en) * 2005-01-04 2005-02-09 Univ Belfast Base stable ionic liquids
US20070101824A1 (en) * 2005-06-10 2007-05-10 Board Of Trustees Of Michigan State University Method for producing compositions of nanoparticles on solid surfaces
FI120265B (fi) * 2005-07-14 2009-08-31 Kemira Oyj Tärkkelyksen eetteröintimenetelmä
US20070129568A1 (en) * 2005-12-06 2007-06-07 Ngimat, Co. Ionic liquids
CN1958574B (zh) * 2006-11-16 2012-05-02 中国科学院长春应用化学研究所 一种离子液体的制备方法
CN100443157C (zh) * 2006-11-16 2008-12-17 中国科学院长春应用化学研究所 一种微波连续反应设备的应用
CN100455584C (zh) * 2006-12-13 2009-01-28 辽宁大学 微波辅助离子液体中合成四苯基卟啉的方法
EP1950196A1 (fr) * 2007-01-29 2008-07-30 Boehringer Ingelheim Pharma GmbH & Co. KG Procédé de fabrication d'hexafluorophosphates d'ammonium
US10174129B2 (en) 2007-02-14 2019-01-08 Eastman Chemical Company Regioselectively substituted cellulose esters produced in a carboxylated ionic liquid process and products produced therefrom
US8148518B2 (en) * 2007-02-14 2012-04-03 Eastman Chemical Company Cellulose esters and their production in carboxylated ionic liquids
US9834516B2 (en) * 2007-02-14 2017-12-05 Eastman Chemical Company Regioselectively substituted cellulose esters produced in a carboxylated ionic liquid process and products produced therefrom
KR101547874B1 (ko) 2007-07-26 2015-08-27 아지노모토 가부시키가이샤 수지 조성물
US8188267B2 (en) 2008-02-13 2012-05-29 Eastman Chemical Company Treatment of cellulose esters
US9777074B2 (en) 2008-02-13 2017-10-03 Eastman Chemical Company Regioselectively substituted cellulose esters produced in a halogenated ionic liquid process and products produced therefrom
US8158777B2 (en) 2008-02-13 2012-04-17 Eastman Chemical Company Cellulose esters and their production in halogenated ionic liquids
US8354525B2 (en) * 2008-02-13 2013-01-15 Eastman Chemical Company Regioselectively substituted cellulose esters produced in a halogenated ionic liquid process and products produced therefrom
KR100970480B1 (ko) * 2008-09-03 2010-07-16 삼성전자주식회사 마이크로파와 음이온을 이용한 액체 매질 가열방법, 음이온이 첨가된 생물학적 분석장치 및 액체 매질 가열용 용액
MX2008006731A (es) * 2008-05-26 2009-11-26 Mexicano Inst Petrol Liquidos ionicos en la desulfuracion de hidrocarburos y procedimiento de obtencion.
US8980196B2 (en) * 2009-03-13 2015-03-17 University Of Utah Research Foundation Fluid-sparged helical channel reactor and associated methods
US8524887B2 (en) * 2009-04-15 2013-09-03 Eastman Chemical Company Regioselectively substituted cellulose esters produced in a tetraalkylammonium alkylphosphate ionic liquid process and products produced therefrom
CN102477044A (zh) * 2010-11-26 2012-05-30 苏州凯达生物医药技术有限公司 导电高分子聚3，4-乙烯二氧噻吩(pedot)的单体3，4-乙烯二氧噻吩(edot)的合成方法
US9796791B2 (en) 2011-04-13 2017-10-24 Eastman Chemical Company Cellulose ester optical films
US8563463B1 (en) 2012-06-29 2013-10-22 Nissan North America, Inc. Rapid synthesis of fuel cell catalyst using controlled microwave heating
WO2014018586A1 (fr) * 2012-07-24 2014-01-30 The Board Of Trustees Of The University Of Alabama Procédé d'électrofilature de fibres de chitine à partir d'une solution de biomasse chitineuse et fibres et articles obtenus par ce procédé
ES2906062T3 (es) * 2013-11-29 2022-04-13 Proionic Gmbh Procedimiento para la unión de un material termoplástico por medio de radiación de microondas
WO2015102234A1 (fr) * 2013-12-30 2015-07-09 부산대학교 산학협력단 Developpement de synthese en enceinte unique de liquide ionique anhydre au moyen d'orthoester de trialkyle
US10100131B2 (en) 2014-08-27 2018-10-16 The Board Of Trustees Of The University Of Alabama Chemical pulping of chitinous biomass for chitin
US10927191B2 (en) 2017-01-06 2021-02-23 The Board Of Trustees Of The University Of Alabama Coagulation of chitin from ionic liquid solutions using kosmotropic salts
WO2018236445A2 (fr) 2017-03-24 2018-12-27 The Board Of Trustees Of The University Of Alabama Matières composites de type particules métalliques-chitine et leurs procédés de fabrication
CN108620428B (zh) * 2018-04-08 2020-12-18 王微静 一种基于离子液体的土壤重金属淋洗液及其制备方法
CN112724154B (zh) * 2019-10-28 2022-06-07 中国石油化工股份有限公司 一种异山梨醇酯增塑剂及其制备方法
CN114656354B (zh) * 2022-04-28 2023-12-29 河北科技大学 一种醋酸正丁胺离子液体的制备方法
EP4539986A2 (fr) 2022-06-16 2025-04-23 Fundación Centro de Investigación Cooperativa de Energías Alternativas, CIC Energigune Fundazioa Système catalytique contenant des liquides ioniques et procédé de production d'hydrogène à partir de matières plastiques à l'aide dudit système catalytique
CN116769110A (zh) * 2023-07-17 2023-09-19 李小平 一种高熔体强度聚丙烯树脂及其制备方法

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2784789B2 (ja) * 1989-03-27 1998-08-06 山本化成株式会社 ２―アルキルアントラキノンの製造方法
FR2663933B1 (fr) * 1990-06-27 1994-06-17 Beghin Say Sa Nouveau procede de preparation du 5-hydroxymethylfurfural a partir de saccharides.
US5883349A (en) * 1993-09-24 1999-03-16 Duquesne University Of The Holy Ghost Method and apparatus for microwave assisted chemical reactions
CN1123031A (zh) * 1994-02-10 1996-05-22 英国石油化学品有限公司 离子液体
GB9402612D0 (en) * 1994-02-10 1994-04-06 British Petroleum Co Plc Ionic liquids
US5827602A (en) 1995-06-30 1998-10-27 Covalent Associates Incorporated Hydrophobic ionic liquids
SE509731C2 (sv) * 1996-05-14 1999-03-01 Labwell Ab Metod för palladium-katalyserade organiska reaktioner innefattande ett uppvärmningssteg utfört med mikrovågsenergi
US5731101A (en) 1996-07-22 1998-03-24 Akzo Nobel Nv Low temperature ionic liquids
JP3069677B2 (ja) * 1996-07-25 2000-07-24 工業技術院長 有機カルボン酸エステル化合物の製造方法
KR20000029759A (ko) * 1996-08-01 2000-05-25 트롤리에 모리스;다니엘 델로스 치환디플루오로메틸기의그라프트화공정
FR2751961B1 (fr) * 1996-08-01 1998-09-11 Rhone Poulenc Chimie Procede pour la synthese de derives organiques oxysulfures et fluores
JP2000516237A (ja) * 1996-08-16 2000-12-05 ユニケマ ケミー ベスローテム ベンノツトシヤツプ 脂肪酸誘導体の製造方法
CN1278238A (zh) * 1997-10-13 2000-12-27 探索国际股份有限公司 弗里德尔－克拉夫茨反应中或有关该反应的改进

Also Published As

Publication number Publication date
NO20015578L (no) 2002-01-24
NO321962B1 (no) 2006-07-31
US6596130B2 (en) 2003-07-22
DE60013832D1 (de) 2004-10-21
CN1361716A (zh) 2002-07-31
JP2003500460A (ja) 2003-01-07
EP1194227A1 (fr) 2002-04-10
NO20015578D0 (no) 2001-11-15
WO2000072956A1 (fr) 2000-12-07
AU4604600A (en) 2000-12-18
CA2374251A1 (fr) 2000-12-07
ES2228518T3 (es) 2005-04-16
EP1194227B1 (fr) 2004-09-15
ATE276043T1 (de) 2004-10-15
CN1188211C (zh) 2005-02-09
US20020056633A1 (en) 2002-05-16
DE60013832T2 (de) 2005-09-29
AU774290B2 (en) 2004-06-24

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